Azoxystrobin, chemically named methyl (E)-2-(2-(6-(2-cyanophenoxy)pyrimidine-4-oxy)phenyl)-3-methoxyacrylate, is the first commercialized β-methoxyacrylate-based fungicide that was developed by Zeneca Inc. It exhibits a fungi suppressing activity by acting as a mitochondria respiration inhibitor, i.e. inhibiting the respiration of mitochondria by impeding electron transfer between cytochromes b and C1. Azoxystrobin is a highly effective and broad-spectrum fungicide with activity against almost all pathogenic fungi including Oomycetes, Phycomycete, Ascomycota and Deuteromycetes. And it can be used on crops like grain, rice, grape, potato, vegetable, fruit trees, beans and so on by stem or foliar application, or seed treatment. For the above reason, there are many patent documents reporting its synthesis methods, e.g. EP-A-0382375A, WO92/08703A1 and GB229174, etc.

The preparation methods which have been reported as yet can be classified into two categories:
(A) O-hydroxyphenylacetic acid, as the starting raw material, is dehydrated to obtain benzofuranone followed by introduction of a methoxymethylene group to benzofuranone's side chain with the use of trimethyl orthoformate or methyl formate. Then the resulting intermediate is condensed with 4,6-dichloropyrimidine and with o-cyanophenol to obtain azoxystrobin. The key point of this method lies in the methoxymethylenation of α-methyl in the benzofuranone and its stability in subsequent reactions. The document first reporting this method is Australian Journal of Chemical, 26(5), 1079-91, 1973 and Journal of Organic Chemistry, 40(24), 3474-80, 1975.
(B) O-hydroxyphenylacetaldehyde is used as the starting material, and the protection of phenolic hydroxy first by benzyl group and a series of reactions are conducted to obtain methyl 2-benzyloxyphenylacetate. Then methoxymethylenation reaction is carried out by reacting methyl 2-benzyloxyphenylacetate with methyl formate in the presence of sodium methoxide. The resulting product is condensed with 4,6-dichloropyrimidine and then with o-cyanophenol to obtain azoxystrobin.
Method (B) is the first introduced synthesis route as well as the first reported synthesis method by patent documents. Despite the synthesis of the product being achieved, it involves additional processes including protection of starting material, de-protection of intermediate product, and a series of conversions.